Taburnaemines A–I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from Tabernaemontana corymbosa
| Autor: | Yu Zhang, Yu Xi Yuan, Ling Li Guo, Kuo Hsiung Lee, Xiao Nian Li, Masuo Goto, Xiao-Jiang Hao, Susan L. Morris-Natschke |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Tabernaemontana Pharmaceutical Science 01 natural sciences Article KB Cells Analytical Chemistry Indole Alkaloids Structure-Activity Relationship Drug Discovery Structure–activity relationship Cytotoxic T cell Moiety Humans heterocyclic compounds Tabernaemontana corymbosa Pharmacology biology 010405 organic chemistry Chemistry Alkaloid Organic Chemistry biology.organism_classification Antineoplastic Agents Phytogenic 0104 chemical sciences Plant Leaves 010404 medicinal & biomolecular chemistry Complementary and alternative medicine A549 Cells MCF-7 Cells Molecular Medicine Drug Screening Assays Antitumor Human cancer |
| Zdroj: | J Nat Prod |
| Popis: | Nineteen vobasinyl-ibogan-type bisindole alkaloids, including nine new compounds, taburnaemines A–I (1–9), were isolated from the twigs and leaves of Tabernaemontana corymbosa. The structures and absolute configurations of the new alkaloids were determined by a combination of MS, NMR, and ECD analyses. Alkaloids 1–5 contain a rare 1,3-oxazinane moiety in the vobasinyl unit, while 6 has an uncommon 1,3-oxazolidine moiety in the iboga unit. The absolute configurations of alkaloid 1 and the known alkaloid tabernaecorymbosine A (10) were confirmed by single-crystal X-ray diffraction analysis. All of the bisindole alkaloids, except 2 and 16′-decarbomethoxytabernaecorymbosine A (14), showed antiproliferative activity (IC(50) 2.6–9.8 μM) against several human cancer cell lines, including A-549, MDA-MB-231, MCF-7, KB, and P-glycoprotein-overexpressing multidrug-resistant KB cells. The preliminary structure–activity relationship correlations are also discussed. |
| Databáze: | OpenAIRE |
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